Squire Patton Boggs director Jon Chesman offers his take
“Commercial awareness is something that almost every firm will expect their trainee candidates to be able demonstrate,” says Jon Chesman, a director in the restructuring and insolvency practice group at Squire Patton Boggs in Leeds. “Students are aware that firms want it, and it is something we look for, but it can sometimes seem to be an abstract concept, which is not massively helpful.”
Chesman describes his own route into the profession as “one of the more traditional ones”. He studied law at the University of Leeds, completed the LPC and did a summer vacation scheme with the firm during university. He started his training contract there in 2013 and qualified in 2015. “Squire is the only firm I have ever worked at,” he says.
So what does commercial awareness actually mean? “At its most basic level, if someone is “commercially aware”, they are interested in business generally and has knowledge of what is going on in the business world,” he explains. “That way, when you are performing your role as a solicitor at a major law firm, you come across as clued up on what the firm is doing on a business level and what our clients are doing.”
That means understanding clients’ businesses, including their priorities, the issues they face and how the firm can help them achieve their goals. It also means understanding the law firm itself, from how it makes money to who its competitors are.
With seniority comes the ability to assess and value risk, for example advising a client on the risks of conceding an amendment to a clause in a contract the other party will not accept. Chesman is clear that this would not be expected of a graduate or necessarily a trainee.
Sometimes, he says, candidates think the expectations regarding commercial awareness are higher than they needs to be. As part of the Emerging Talent Leadership Team in Leeds, Chesman conducts training contract interviews and sees candidates wonder whether they need to know what the stock market closed at last night, or the exact price of a barrel of oil. “While knowing that is good, that level of detail is not really required,” he says. “It requires a high-level, broad analytical approach rather than focusing on one or two issues really deeply.”
His restructuring work gives him a particular view of business challenges. His team is generally brought in when businesses are under stress or distress and need a turnaround plan or business rescue, often advising boards of directors. He says that “having an advisory seat at that board table allows you to appreciate the specific problems businesses are confronting”.
Asked for the three themes that will matter most to clients over the next year to eighteen months, Chesman offers, “in no particular order”, AI, geopolitical uncertainty and cost pressures.
On AI, he says that “absolutely everybody is talking about AI at the moment” and that it is a key investment decision for boards, who must decide whether to be at the forefront of AI integration and therefore potentially accept higher investment costs than competitors with the aim of getting ahead, or to take a more conservative approach and “follow the market” . For lawyers, he says, it is “another tool that, when used properly, acts like a personal assistant to speed up certain tasks”, though confidentiality, accuracy and data protection issues mean firms must choose their tools carefully. His own firm recently announced that it is using Harvey as its main AI platform. Work such as reviewing hundreds of contracts for change-of-control provisions, or disclosure exercises in litigation, which traditionally would have been time-intensive “could be accelerated significantly with AI”.
The lawyer’s role still sits on top of any AI tool, with human analysis and problem-solving remaining crucial to assess risk and advise clients. But clients will rightly expect turnaround times for certain tasks to fall from days to hours, which also affects traditional hourly billing models. Is AI about better work or just faster work? “It is definitely a way of making things more efficient,” Chesman says. Whether it improves the work depends on the tools, prompts and inputs. He warns that “poor inputs will yield poor outputs”.
The second theme is geopolitical uncertainty. Since 2020 and the start of COVID, he says, many traditional norms have been upended, which businesses have had to adapt to very quickly. He also cites current challenges, such as disrupted oil flows through the Strait of Hormuz, changes to the US tariff regime and volatile energy markets. He sees no sign of this changing in the near term.
The third is cost pressures squeezing profit margins. In the UK, the cost of labour has risen because of increases in the minimum wage and national insurance contributions, and energy spikes and supply chain disruption push up other costs. While many businesses can currently pass costs on, certain sectors such as retail and hospitality face fierce competition and price-sensitive customers. Construction often works on fixed-price contracts, where rising costs erode margins, and “a single bad contract can have a significant impact”.
What does good commercial awareness look like? In an interview, Chesman says, “it comes across clearly whether a candidate is genuinely interested in business or has merely read a couple of recent articles on the BBC”. Good candidates think analytically about a particular commercial issue e.g. what oil price volatility does to businesses in specific sectors, how that affects the firm’s clients and what it means for the firm. They also research the firm and its markets.
Applicants keen to discuss a business failure or restructuring can stand out by “getting to the underlying causes”. Was it a specific challenge, such as one unprofitable contract, a customer or supplier failure, or a sector-wide issue? If the business was rescued, “look at the insolvency process used and its impact on different stakeholders”, Chesman says. Shareholders are usually left with nothing in an administration, but creditors fare differently depending on whether they are secured or unsecured and what happens to the underlying business e.g. did someone acquire the business, in which case customers and suppliers may still be able carry on trading with that business under new ownership, and employees’ roles may be preserved. . “Breaking down the situation across those stakeholder perspectives would be very impressive in an interview,” he says.
The common mistakes? “Candidates often get too granular in the detail of one specific story, pinning all their hopes on it arising in the interview, and find themselves stuck if it does not.” The other is failing to take the analysis “through steps two and three: linking the issue to what it means for our clients, and then considering what that means for us as a legal business”.
As for why he is at Squire Patton Boggs, Chesman points to the firm’s global footprint, with a significant restructuring presence in the US, Europe and Australia. This allows it to handle “genuinely global cross-border restructuring matters, which are often larger, more challenging, but more interesting”. The Leeds team works as part of a national practice, and he is currently collaborating with the London team on a major project.
Finally, he has a myth to bust. Restructuring and insolvency lawyers are not only given a call when a business is about to run out of cash. “When engaged early enough to address problems, you can often avoid the need for a formal insolvency process altogether,” Chesman says. “We add real value to struggling businesses well before they reach the precipice of failure.”
Jon Chesman will be speaking at The Big Commercial Awareness Themes of 2026-27, a virtual student event taking place on Friday 6 November from 2pm to 4:30pm, along with representatives from other top firms. Secure your place now.
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